Manifesto

The messy middle

Every leader, every organisation, every human life moves in S-curves.

You begin something new. A role, a strategy, a company. At first it’s hard, and you feel like you are going backwards. Then something clicks, momentum builds, and for a while things work. You grow, you succeed, you get good at what you do. Then, gradually or suddenly, the curve flattens. What got you here stops getting you further. The energy of this particular chapter is spent.

Charles Handy mapped this in the 1990s and called it the sigmoid curve. I first met it at London Business School – the school Handy helped found – and by then I had already been riding these curves for years without knowing they had a name.

More than thirty years in technology businesses. A search fund launched in the teeth of the credit crunch, two weeks before the birth of my fourth child, to do something almost nobody in Europe had heard of at the time. The payments business I found, bought, transformed and sold. An online training side hustle that taught me mostly what doesn’t work. A B2B tech marketplace built to global reach and shut down by war. And since 2023, this curve: coaching, advisory, boards, a couple of chair roles, investing.

So none of what follows is theory I am recommending from a safe distance. It is terrain I have crossed repeatedly, and rarely elegantly. I am better at these passages than I used to be. They have not become comfortable. I am in one now.

Handy’s radical insight: the time to start the next curve is before the first one ends. When you still have energy, momentum and resources in hand. Not when you are already in decline and desperate. The leaders and organisations who sustain relevance are the ones who see the inflection point coming and make the jump.

The part that is seldom talked about is the jump itself, and the messy middle it puts you in.

What actually happens in the gap


Between letting go of the first curve and finding your footing on the second, there is a space. A passage. An in-between.

It’s what anthropologists call liminal space – from the Latin limen, meaning threshold. You’re neither here nor there. What worked before has stopped working. What comes next hasn’t taken shape yet. The old identity, the old playbook, the old way of operating – none of it applies, and you know it. But the new one isn’t available yet either.

This is the messy middle.

It is deeply uncomfortable. Not because something has gone wrong – because this is what transition feels like from the inside. The disorientation is not a sign of failure. It is the process doing its work.

Most people read this discomfort as stuckness. In my experience, they are almost never stuck. They are lost. Stuck means inertia: you haven’t let go, the first curve still has its hooks in you. Lost means movement without orientation: you have committed, you are in motion, but you can’t yet see the landmarks. Lost people don’t need to start moving. They need to find their bearings and keep going.

You don’t need to see the other side to navigate toward it. You need enough orientation to hold a consistent direction – find the river, follow the river to the road, follow the road to something recognisable. Getting unlost is an active, dynamic process, not a passive waiting for clarity to arrive.

Why this is now a leadership-critical skill


Early in my career, the big transitions arrived a decade or so apart, with time to recover, reorient and rebuild before the next inflection. They did not stay that way. The gaps between my own went from twelve years to seven, from seven to five, from five to three. Faster each time, and increasingly on top of one another.

The same acceleration is running through every leadership team I work with. The cycles are compressing. Leaders who used to face one significant transition every ten years now face several at once, with barely a breath between them. The curves are stacking. Liminality is becoming less of an exceptional passage and more of a permanent condition of leadership at this level.

This changes what the most valuable leadership skill actually is.

Knowledge is no longer the scarce resource. AI can synthesise and surface information faster than any of us. Knowledge has been democratised. It is effectively free. I built a career on knowing things, and I am telling you that advantage is gone – for me, and for you.

What remains scarce is the capacity to execute in conditions of uncertainty. To keep moving when you can’t see the next landmark. To stay present and functional when the nervous system is screaming for the safety of the familiar. To complete the passage you’re already in, rather than retreating to the comfort of the one you’ve already left.

This is wisdom, not knowledge. And it lives in the body as much as in the head – a lesson I came to later than I would have liked.

What execution in liminality actually requires


Naming the passage is the first move. It shifts the experience from I am broken and failing to this is what transition feels like, and there is a way through. That reframe alone changes what is possible.

But naming it isn’t enough. You still have to move.

The instinct, almost universally, is to push harder with what used to work, or to retreat. I have done both, more than once. Pushing harder is how you exhaust yourself doing the wrong things with great intensity. Retreat is not actually available – the ships are burned, the first curve is spent, and going back only returns you to what was already ending.

The only direction is forward. Forward asks four things of you.


Stay present in the discomfort long enough for it to do its work. Not managing it, not eliminating it, not outrunning it. What you carry out of a messy middle is different from what you carried in – the identity, the capacities, the leadership itself. That transformation takes time inside the crucible.

Read the system and act on partial information. You will never have complete visibility in liminality. Waiting for certainty before moving is what gets people genuinely stuck. Find a bearing from the available landmarks, commit to a direction, adjust as you go.

Regulate under sustained pressure. This is more physical than it sounds. Under chronic uncertainty the nervous system shifts into threat response, and from that state good decisions get harder, relationships get harder, and the cognitive flexibility you need most becomes least available. The leaders who move well through these passages do not feel less pressure. They have built the capacity to carry more of it.

Let go of what you carried in. The hardest part, every time. The identity, the assumptions and the methods that built the first curve feel like assets. They are. They were. The second curve needs a different version of you, and that version only emerges once the old one is genuinely set down. You cannot drag the past into the future and call it transformation.

What this means going forward


The leaders who will navigate the next decade well are not the ones with the most knowledge or the most sophisticated frameworks. Artificial intelligence is a better framework repository than any human could be.

They will be the ones who recognise the inflection point before it becomes a crisis. Who begin the next curve with energy still in the current one. Who move through the middle without retreating or collapsing, come out with more capacity than they went in with, and then do it again – sooner, and less disoriented than the last time.

That is the nature of leadership now. Not one big transition carefully managed. A recurring rhythm of them, arriving faster, overlapping more, demanding more of the whole system each time: body, mind, relationships, culture.

Underneath all of it sits something I hear from every leader I work with, in one form or another: how do I actually do this, without it costing everything?

The question isn’t whether you’ll face a messy middle. You’re almost certainly already in one. The question is what you do inside it.

That’s the work I do with leaders. One piece of the passage at a time.

Don’t try it alone


This is yours to do. No one can complete it for you. But it is a mistake to try to do it alone – not a weakness, a miscalculation. The trapeze artist doesn’t catch themselves. The right company doesn’t rescue you from the middle; it keeps you honest inside it, holds the complexity without collapsing it, and stays until the work is genuinely done, and you become ready for what comes next.

If this feels familiar, let’s talk.

Tell me where you are, and let’s find out if we’re the right fit.

This work is yours to do, but I’ll stay with you until it’s done.